SOLIMASTAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H32N4O5
Molecular Weight	408.4919
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@@H]([C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC1=CC=CC=N1)C(C)(C)C)C(=O)NO

InChI

InChIKey=WORSVFBVUCBRIP-VNQPRFMTSA-N

InChI=1S/C20H32N4O5/c1-12(2)11-13(15(29-6)18(26)24-28)17(25)23-16(20(3,4)5)19(27)22-14-9-7-8-10-21-14/h7-10,12-13,15-16,28H,11H2,1-6H3,(H,23,25)(H,24,26)(H,21,22,27)/t13-,15+,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H32N4O5
Molecular Weight	408.4919
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800006529 | https://www.ncbi.nlm.nih.gov/pubmed/14970856

British Biotech was developing solimastat [BB 3644], an inhibitor of tumour necrosis factor and matrix metalloproteinase, as a potential treatment for colorectal cancer, inflammatory bowel diseases and rheumatoid arthritis. BB-3644 is an oral, broad-spectrum matrix metalloproteinase inhibitor (MMPI) structurally related to marimastat and BB-94. It is also >10-fold more active than marimastat in inhibiting the processing of cell-bound TNF-alpha. Solimastat development has been discontinued due to significant musculoskeletal toxicity.

Originator

Approval Year

PubMed

Title	Date	PubMed
Metalloproteinase inhibition augments antitumor efficacy of the anti-CD30 immunotoxin Ki-3(scFv)-ETA' against human lymphomas in vivo.	2004-09-10	15239135
Ongoing trials with matrix metalloproteinase inhibitors.	2000-09	11060801

Sample Use Guides

In Vivo Use Guide

Advanced solid tumours: treatment consisted of twice daily (bd) oral solimastat [BB 3644] for 84 days. The initial dose was 5 mg bd, and subsequent cohorts were treated with 10, 20 and 30 mg bd. In all, 22 patients were enrolled. The dose-limiting toxicity (DLT) was musculoskeletal pain. For 28 days of treatment with BB-3644, 20 mg bd was the maximum tolerated dose (MTD), as at 30 mg bd, six of nine patients developed significant musculoskeletal toxicity by day 28.

Route of Administration: Oral

In Vitro Use Guide

CD30 shedding from the cell line Karpas 299 could effectively be blocked by the hydroxamic acid-based metalloproteinase inhibitor BB-3644 (IC50 = 180 nM)

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:44:15 GMT 2025` Edited by `admin` on `Mon Mar 31 18:44:15 GMT 2025`
Record UNII	414MEG73VU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTANEDIAMIDE, N1-((1S)-2,2-DIMETHYL-1-((2-PYRIDINYLAMINO)CARBONYL)PROPYL)-N4-HYDROXY-3-METHOXY-2-(2-METHYLPROPYL)-, (2R,3S)-

Preferred Name

English

SOLIMASTAT

Official Name

English

solimastat [INN]

Common Name

English

(2S,3R)-3-((1S)-(2,2-DIMETHYL-1-(2-PYRIDYLCARBAMOYL)PROPYL)CARBAMOYL)-2-METHOXY-5-METHYLHEXANOHYDROXAMIC ACID

Systematic Name

English

BB-3644

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1970